Acetone → Diethyl 3,3-dicarboxycyclobutanone

HRID 1005334Notes

Reaction equation

HRID 1005334 reaction equation
CO[C:3]1([O:17]C)[CH2:6][C:5]([C:12]([O:14]CC)=[O:13])([C:7]([O:9]CC)=[O:8])[CH2:4]1.[C:19]1(C)C=CC(S(O)(=O)=O)=C[CH:20]=1.C(=O)(O)[O-].[Na+].O.[CH3:36][C:37](C)=O>>[CH2:19]([CH:4]1[C:3](=[O:17])[CH:6]([CH2:36][CH3:37])[C:5]1([C:12]([OH:14])=[O:13])[C:7]([OH:9])=[O:8])[CH3:20]

Participants

6

Reactant 5

HCID 180Acetone2×HCID 962WaterHCID 6101p-Toluenesulfonic acid2×HCID 516892Sodium BicarbonateHCID 14143444Diethyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate

Product 1

HCID 131721779Diethyl 3,3-dicarboxycyclobutanone

Conditions

Temperature
65 °C

Procedure

A stirred mixture of diethyl 3,3-dimethoxycyclobutanedicarboxylate (10.36 g, 39.8 mmol) in acetone (95 ml) and p-toluenesulphonic acid (1.38 g, 8.02 mmol) was heated to 65° C. overnight. Further p-toluenesulphonic acid (200 mg, 1.16 mmol) and acetone (15 ml) were added and the temperature raised to 75° C. for 2 hours. The reaction was cooled to room temperature. The mixture was neutralised with aqueous sodium bicarbonate. Water (15 ml) was added and then extracted with dichloromethane (3×10 ml). The extracts were dried over magnesium sulphate, filtered and evaporated in vacuo to give a brown oil. The crude oil was distilled (bulb-to-bulb) to give diethyl 3,3-dicarboxycyclobutanone as an oil, b.p. 150-155° C./0.1 mm.

Workup

  1. temperaturethe temperature raised to 75° C. for 2 hours
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with dichloromethane (3×10 ml)
  4. dry with materialThe extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a brown oil
  8. distillationThe crude oil was distilled (bulb-to-bulb)

Sources & evidence

ORD record
ord-c58846eeb07b493dbda6bdf2e198f6b8
Source dataset
uspto-grants-2000_04
Patent number
US06054448

Reaction notes

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